


Saddle Me Up

by casstayinmyass



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Bottom Dean, Cheating, Cheating Dean, Cock Slut Dean, Coda I Guess, Cute Confession, Dean Has a Cowboy Kink, Doggy Style, Dominant Elias, Episode: s06e18 Frontierland, Established Castiel/Dean Winchester, Horny Dean, It Was Supposed To Be A Hot One Shot But Feels Got Involved, Jealous Castiel, M/M, PWP, Plot What Plot/Porn Without Plot, Rough Sex, Spit As Lube, Top Elias Finch
Language: English
Status: Completed
Published: 2016-01-29
Updated: 2016-01-29
Packaged: 2018-05-16 23:45:40
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 4,039
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5845561
Author URL: https://archiveofourown.org/users/casstayinmyass/pseuds/casstayinmyass
Summary: <blockquote class="userstuff">
              <p>When Dean went back in time with his brother to the old west to collect some Phoenix ashes, he didn't expect to find the sexiest cowboy he had ever seen there...</p>
            </blockquote>





	Saddle Me Up

**Author's Note:**

> Yeah, so, I was watching Frontierland again, and... this happened...
> 
> \\(^^)/ 
> 
> I always thought these two would be hot together haha.

-0-0-0-

Dean Winchester loved old western movies; it was futile for him to deny it. He loved the _music_ , the sets, the campy one-liners that set his blood on fire... and, something else on fire too, if it happened to be the sexy male lead muttering them in a deep drawl.

Yes, okay? He had a thing for those strong, silent type men in cowboy movies. It was a thing, a thing he couldn't get over since his dad had taken him and Sam to see Tombstone when it came out. Dean was fourteen at the time, and he just couldn't get Kurt Russell's twang out of his head that night. It also didn't help matters much that he had raging hormones at the time, but eh, semantics.

 He had never really lost his love of those movies. When they were mentioned, his eyes would light up like a Christmas tree, and for a second, he didn't care that Sam was rolling his eyes at him. Westerns sometimes felt as if they reflected his own life- the dangerous, town-skipping stranger who could charm anyone they wanted would roll in, take care of the baddies, and roll out with just as much suave as ever. Dean tried his best to emanate that in what they did for a living.

Needless to say, Dean was overjoyed when he found out they were going to have to go back in time to the old west.

"You have a fetish," Sam told Dean, and Dean pursed his lips.

"I just like the genre, okay?"

"Yeah, sure- you even know what that stupid monkey's name is!"

"C-Clyde," Dean muttered timidly in defense, and Sam smirked.

"See?"

"Oh shut up, bitch. You've got plenty of fetishes of your own! Remember that time I walked in on you whacking off to a book?"

Sam's face immediately paled, then became red in seconds. "I wasn't- it was the _content_ of the book... y'know what? I don't have to explain myself to you. The point is, you know you want to sleep with, like, every saloon girl in every cowboy movie."

Dean laughed nervously. "Yeah... every saloon girl..."

He did find the girls in the westerns attractive- sexy, even. Many a time had he jerked off thinking of a woman with a cowboy hat and assless chaps begging to ride him like a horse.

It's just... sometimes... Sam Elliot might make his way into those fantasies at some point... or maybe Eastwood himself, doing that squint, oh-

Dean swallowed, looking around as if someone could see his thoughts. Evidently, Cas may have caught one or two of them, because he looked extremely irritated.

"You've got twenty four hours," Cas enunciated, almost biting the statement out, "I trust you'll use the time _wisely_."

Dean noticed this pointed statement with a weary glance to his boyfriend, but Sam didn't, so Cas just went on to send them back in a quick flash and a rush of cold air.

Suddenly, they were in 1861, the day of March 5th. Dean grinned, looking around.

"Dude... awesome!"

"Right," Sam frowned, looking down to avoid stepping in any horse crap, "Let's go, cowboy."

Dean didn't drop his grin as they walked into town... and he most certainly didn't when he saw the sexiest man they had seen back then (men and women, Dean was quickly noticing, were lacking in attractive points).

Unfortunately for Dean, this man was getting hanged presently.

"Wow," Sam cringed, "Hello, authenticity..."

Dean licked his lips, and as the tall stranger stood on the wooden platform, he looked down at Dean, staring a little bit. He looked angry, bitter, vengeful... and surprisingly not scared, as if he _wasn't_ about to be publicly executed.

"Huh," Dean muttered, and finally broke his stare to keep walking. As he walked, he couldn't shake the chill he had; those eyes were haunting.

They walked into the sheriff's office when they found it, since if they run the town, they most likely knew where to find certain people. Dean had to keep reminding himself they were there for the Phoenix and Samuel Colt, not to fanboy and go weak at the sight of the first cowboy he saw.

They walked into the office, and found three older men, sitting around and chewing tobacco.

"Uh... hey there," Sam said, tipping his hat.

"Hello," the sheriff said, cordially nodding back, "You boys're from outta town, huh?"

"Yessir," Sam replied, and Dean stepped in.

"We're actually Marshalls, brothers. The name's Eastwood. I'm Clint, he's... Wedge."

Sam would be saving his bitchface for later for that one.

"We're lookin' for a man," Dean said, tilting up his hat a little in an attempt to look cool (and failing).

"Yeah, I bet," the mayor chortled, and Sam turned to him quickly. Dean gulped, and reddened.

"You're too _clean_ ," the mayor continued, and shook his head.

Dean sniffed, and blinked a couple of times, looking down at his clothes he had gotten from some cosplay store.

"Dirtier than it looks..." he muttered, and Sam nudged him.

"Okay, we're looking for a man named Colt," the younger brother supplied, and the sheriff told them, helpfully, to go find Lew's Saloon and ask there.

"We don't take names," the judge added before they left, giving a near-toothless grin, "We just bring 'em to justice."

By the cackle he gave, Dean shuddered to believe him.

They headed over to the saloon, and there, Dean saw two beautiful girls.

"Damn," he smirked as they sauntered up to them. Momentarily, he had forgotten tall dark and handsome out in town. And, well, Cas.

"Hello," one with honey blonde hair cooed, and the other brunette practically pushed her breasts in his face as she asked, "You from out of town, sugar?"

"Yeah," Dean breathed, unable to tear his eyes away from her massive rack. The only thing that pulled him out of their clutches was Sam, quite literally doing so.

"Focus?" he reminded Dean, and Dean rolled his eyes, turning to the bar.

"Hi," he said, "You Lew?"

"The one and only," the barkeep said, polishing a glass, "What can I get for you boys?"

"I'll have your top shelf whiskey," Dean grinned.

Lew stared at him. "We've only got one shelf."

Dean blinked, and nodded. "Oh, and he'll have a sarsaparilla," he added quickly, before Sam could speak. Another bitchface coming.

"Hey Lew," Sam said, "Do you happen to know of a man named Colt?"

Lew nodded. "Oh yeah. Colt comes in here all the time, he does. Regular drunk, the townspeople say... used to be a great weapon maker back in the day. Oh yeah, you can find him here, alright."

Dean nodded as well. "Any idea when he usually comes in?"

"Well, I invite ya to stick around and wait for him. He usually comes in for the evenings."

The two brothers nodded, and went to sit down. Four hours later, the sun was almost down, and Colt had still not shown up.

"I'm thinkin' this is a bust," Dean muttered, and Sam sighed, huffing in agreement.

"You should stay here, though... just in case. I'll go check on the local graveyard, see if there are any pointers to the resident Phoenix."

Dean nodded reluctantly, and flagged Lew for another (terrible) whiskey.

The sun went down further, dropping below the prominent mountainous horizon, and all too soon, it was night time.

"Dammit," Dean cursed under his breath. They basically had until noon the next day to find this Phoenix and gank the son of a bitch, which seemed virtually impossible. Now, Dean was well on his way to getting drunk on gasoline-alcohol, and Sam was probably nowhere near finding any concrete dirt.

Dean looked up, decidedly going to call it a night soon, but his eyes found something disturbing to say the least.

The man that they had watched hang by the neck that afternoon was sitting at the bar, his hat shadowing his eyes.

Dean did a double take, wondering if he was drunker than he initially thought, but he couldn't be hallucinating something so real... so intense.

Something compelled the man to look over, and his eyes, Dean realized, were a dark shade of brown, so brown they looked black. Not demon black, just... mysterious.

He gulped down the rest of his whiskey, and looked away. The next thing he knew, he was swinging himself up, and sauntering over to the bar.

"Well howdy there, partner. You look like you need a drink." The man, who was indeed Elias, looked up. When he realized who it was that had approached him, he nodded a little, disregarding Dean's strange greeting and opting to accept. "Lemme get it for you," Dean smirked, and patted the bar. "Lew! One more whiskey!"

Lew shrugged, and sent a shot spiralling down to them. Elias hesitated, then nodded at Dean in thanks.

"'Preciate it," he mumbled, taking a sip.

"I'd say you really did need that," Dean chuckled, "As far as I'm concerned, you died this afternoon."

Elias smirked a little. "Yeah, well... that's a sort of problem I have."

"I bet you don't have problems in other areas," Dean whispered, and Elias froze, staring at Dean.

 _Right,_ Dean's mind told what was left of his consciousness, _it's 1861. People don't take too kindly to this sort of thing._

"I only meant gunslinging," Dean muttered, exhaling, and Elias turned back to his drink.

Dean sat next to him, and Elias eventually turned again. "Who are you?"

"D- uh, Marshall, uh... Eastwood."

Elias nodded, and finished his drink.

"You look experienced with tippin' back a glass," Dean said, turning to him, and Elias shrugged.

"My wife died. That's enough reason to tip back an entire bottle."

Dean watched the stubble move as the man talked, and wanted nothing more than to lick it... to lick his strong jaw...

 _But... Cas,_ Dean thought with a lip bite, _he'd have my ass if he found out I..._

"You tryin' to get us killed?" Elias muttered, and Dean was caught off guard.

"Huh?"

"You're starin' at me like a goddamn queer."

"I..."

"See, if you're gonna do it, do it where no one can watch."

Dean shuddered a little. "S that why your killed your wife?  You're secretly into guys?"

"You talk any louder, I'll have to shoot you," Elias warned, and Dean laughed.

"I didn't kill her," Elias finally said, "but... that's another story for another time."

The grumble and scowl that came out of him after signified something horrible had happened that he had been blamed for. But hey- who was Dean to deem this man innocent? He was being hanged earlier, for christsake. He panicked a little, wondering why he was suddenly so turned on by flirting with a dangerous cowboy. A real cowboy, with stubble and dark eyes, and flexing forearms as he drowned his sorrows, and Dean wanted to see what was under those pants pronto. The thing was, the time barrier... law was different back then, and Dean didn't want the dude to get hanged a second time for sodomy. _But hey,_ Dean figured, _I'm never gonna see this guy again._ That much was certain, and Cas might never find out... so he might as well go for it.

"I know this kinda stuff ain't real popular, or, uh... celebrated," Dean said quietly, in a low voice, "But do you wanna get outta here?"

The guy just slammed another drink down. "That a threat?"

"No, no!" Dean tried again quickly, "No. I'm asking... maybe, if you wanna... get outta here together?"

It took Elias a moment to process, then his eyes narrowed.

"Huh," he muttered, and eyed Dean."What town d'you say you were from?"

Dean swallowed. "Uh... Kansas?"

Elias hummed, a sound that made Dean want to moan. God, it embarrassed him how strong his sex drive was sometimes.

As Elias stared at him curiously, Dean knew he had made a mistake. He would be thrown out of town... he would be hanged now, for fuck's  sake. Then Elias beckoned him closer. Dean was waiting for a sharp rejection and a threat to get out before he'd shoot him, but he got something completely different.

"So you're lookin' for someone to rough you up, s'at it?"

Dean blushed, and looked at his feet.

"I guess..."

"You guess?"

"Okay, yes. That's what I want," Dean admitted. "Unless... you-"

Dean faltered as he stared at Elias' face, the man's eyebrows raised. "Do I look like I take dick to you?" Dean swallowed again, (he was starting to get dry mouth or something),  and felt blood rush to his cock.

"N-no sir," Dean mumbled huskily. Elias hummed again.

"Hmmyeah... keep callin' me that."

Dean shuddered, and leaned in, trailing his lips up the cowboy's ear in a rare streak of confidence.

Elias jerked away, and turned to Dean with narrowed eyes, leaning in close.

"You crazy? Wanna get us both killed, do you?!"

The low drawl of his western accent, paired with those dark eyes staring deep into Dean's soul made Dean all too aware of the uncomfortable tightness of his pants. He rolled his hips against the bar stool for some relief, and Elias got up, slamming down his last shot of whiskey with a sharp bang.

Dean moaned, and Elias grabbed Dean by the collar roughly, shaking him as he dragged him out back of the saloon. There was hardly anyone out this late, and those who were, were high on opium or something, 'cause they were stumbling all over the place.

They made their way to the barn that was sitting alone a few yards away, and Elias swung the door open, shoving Dean inside face first. Dean felt his cock twitch as Elias' footsteps crunched over the hay behind him, the shove getting dirt on his hands and knees. Elias held his neck from behind, and Dean grinned, biting his lip.

"You like it rough, huh, boy?" Elias growled in his ear from behind, and Dean breathed out shakily.

"Please fuck me."

"What a little whore," Elias chuckled, "Never met a _man_ so willing to take another man's cock... guess you find somethin' new every day, now, dontcha?"

Dean moaned, hating how long it was taking to just _get fucked._ He wanted to touch himself so bad, and he reached his hand down, slipping it into his pants and taking his hard cock in hand. With a squeeze just under the head, he felt the throb of arousal, and almost sobbed in desperate plea.

Elias smacked Dean's hand away from himself, and stood him up, pressing him into the barn wall. He yanked down his pants and began rubbing himself against the hunter.

"You want it?" he muttered in Dean's ear, and Dean groaned.

"So fuckin' bad..."

"Good," Elias growled, and took himself out of his pants, slicking up his own length with spit. Dean, for his part, did not expect this man to know how to properly prep another man before sex, so as Elias slicked himself, he began working two fingers into his own hole, stretching as wide as he could before he felt the head of the cowboy's cock stretch him open even more.

"Mmmph," Dean mumbled, and Elias immediately began to move.

"Such a good little slut," he grunted, and Dean panted against the wall, feeling every slap of skin against skin as he got screwed from behind.

"Love your dick... so big inside me," Dean grinned, and that earned him a particularly hard thrust and a slam against the wall.

"You kiss your boyfriend with that mouth?"

"How do you know I have a-?"

"I'm not blind, I can see the bite marks on your shoulders," Elias muttered, tracing over said marks with his fingertips. "What do you think he'd think of all this?"

Dean gulped. "He's not... here right now."

"Well, no shit."

"I mean..."

"Shhh, talkin' time's over, whore," Elias growled, and Dean moaned, rutting against the wall as the other man pounded into him. He saw stars when Elias hit his prostate, and he lifted up his leg, letting himself moan and cry out as the pleasure got to be just about too much.

"Gonna come, pretty boy?" Elias asked, rolling his hips into Dean then snapping them.

"Fuck, yeah- yeah, gotta...come..." Dean choked out, breath hitching.

"Go ahead, then- lemme see your pretty ass clench around my dick."

Dean gasped, and with a surge of fire in his belly, he came hard, shooting all over the wall and his shoes. He felt, seconds later, his ass fill with Elias' cum, and he felt the cowboy pull out.

Dean wriggled uncomfortably, and Elias pointed at him. "Keep that in. Want your boyfriend to find out you've been sleepin' around next time you two have some fun, and I assume that'll be soon, slut like yourself."

Dean bit his lip, and pulled his pants back up, feeling his hole leak. It was uncomfortable, but... strangely arousing.

"We'd better get the hell outta here before someone thinks we're doing something unsavory," Elias said, adjusting his belt.

"Yeah," Dean muttered. The two looked around as they exited the barn, and they were only greeted with the chill of the night and the cry of a whippoorwill.

"That was amazing," Dean mumbled to Elias, the taste of whiskey still strong on his breath.

"Yeah, but don't go runnin' your mouth about it," Elias muttered back, adjusting his hat lower on his head, "Night to you."

Dean nodded, tipping his hat. He might as well find an inn or something to stay at, it was too late tonight for the Phoenix hunting anyway. He'd be up early.

"Night."

They parted, Dean watching Elias walk away with a confident, yet still utterly mysterious stride, and swallowed his guilt at what he had just done as he walked into a motel.

-0-0-0-

"Dean!" Sam said, "Wake up!"

Dean grumbled, and opened one eye. Sam was standing over his bed, looking horribly sleep deprived and frankly, like shit.

"You look like horse shit," Dean voiced, and Sam gave him a bitchface.

"Yeah, well, that's probably because I was actually working all night, instead of sleeping!"

"I was working," Dean said defensively, "Sort of. How'd you find me?"

"There's like, _one_ motel in this entire town," Sam muttered, "Anyway, I did some digging, and found out who the Phoenix is."

Dean sat up a little straighter, frowning. "Okay- who?"

"You remember that guy we saw in town yesterday? The one who got hanged?"

Dean's heart skipped a beat, and the blood drained from his face.

"Uh... yeah."

"So get this- his name is Elias Finch, and he's our guy."

Dean gulped, feeling his throat close up. It all made sense now... Dean wondered why another guy was so willing to do that with him in such a sexually repressive time... monsters obviously don't have social inhibitions.

"U-Um, you sure about that?"

Sam turned to his brother, and frowned in bewilderment. "Dude- I was up half the night looking into it. Yeah, I'd stake my life on it."

Dean felt like he was going to physically be sick. "Just... just gimme a minute, okay?" The older Winchester covered his mouth with his sleeve, and ran to the bathroom. After a few minutes, a flush, and a very confused Sam later, Dean came back out, looking pale.

"Dean, you alright?"

"I'm fine... kinda."

Sam frowned for a second, then it dawned on him as horror overtook his expression.

"Oh god... don't tell me you... you didn't."

Dean winced at him, rubbing the back of his neck, and Sam screwed his face up, balking.

" _Dean!_ "

"What?! He was hot, I was... horny... and drunk... and y'know... it just happened!"

"Oh, Christ, too much info, man... you seriously fucked a Phoenix?"

"Well technically, he fucked me."

"Jesus, didn't need that."

"Just... don't tell Bobby, okay? And most importantly, don't tell Cas!"

"Oh, shit, Cas! That's right... he probably knows, Dean."

"How? It's not like he's been hanging over our shoulders the entire time."

"You have to tell him."

"Why?!"

"Dude, you cheated on a warrior of heaven. Be afraid... be very afraid."

"Really? The Fly reference?"

"Shut up, you love that movie. Anyway, I think you should be honest, you owe him that much."

Dean scowled, and scratched his stomach. "Let's just focus on the problem at hand. You got the colt?"

"Yeah... Colt was a hard guy to get through to, but I got it." Sam gave Dean the guy, and Dean cocked it.

"Let's go kill this son of a bitch."

"Probably not what you called him last night."

"Sam-"

"I bet you begged for it."

"No more than you beg me not to watch westerns. You're a loser, by the way, for not liking westerns."

"Fuck you!"

"He did."

Sam threw his arms up, and stormed out the door. Dean shook his head, and got ready to leave.

By mid morning, they came to the spot they had read about in the journal.... and Elias was right on time, dressed in a dark overcoat and his hat.

The revealed Phoenix stopped in his tracks when he saw Dean with Sam.

"You," he drawled in amusement, "were you spying on me last night, then?"

"Nah," Dean shrugged, "I actually had no idea I was getting banged by a dirty, filthy, disgusting scumbucket of a creature."

"Wow, Dean. You sure know how to love 'em and leave 'em," Sam whispered, and Dean stomped on Sam's boot.

"Yeah," Dean continued, waving his gun, "You were a pretty good lay. But now, you're about to become a _dead_ lay."

He turned to Sam, laughing at his own joke, but Sam did not join in. Dean turned back to Elias, putting on a serious face.

"You can't kill me," the Phoenix growled, "Nothing can."

"Yeah?" Dean asked, "How's this, pal?"

As Dean drew the colt, Elias did as well, but miraculously, Dean was the faster draw, and shot the Phoenix with the special bullet they had put together.

Elias' smug smirk turned into a flash of realization and fear, and he screamed in anguish as his body was overtaken with flashes of red and white. Soon, he was nothing but a pile of black dust on the ground, a cowboy hat overtop it. Interestingly enough, Dean felt no remorse at all, even though he probably still had the dude's cum leaking out of him.

"Huh," Sam said, "That's what I assume you'll look like when Cas finds out."

Dean rolled his eyes over to Sam.

"He won't."

Evidently, a day after the two had been transported back to their own time with the ashes and all, Dean _was_ feeling guilty out of his mind. The only thing to do was tell Cas the truth.

"Hey, um," Dean prayed, looking up as he sat on the motel bed. Sam was out at the store restocking on groceries, so he had the time alone to do this.

"Cas? Babe, I need to, uh... talk to you."

There was a whoosh of feathers, and Cas appeared on the bed opposite Dean.

"What is it, Dean?"

Hearing the sheer concern in his voice made Dean's stomach churn even more. "I, uh... I've got somethin' to tell you. In 1861, I- heh, you don't get to start a sentence like that everyday- I, kinda... like... had sex with the guy we were supposed to gank."

"The phoenix," Cas clarified.

"Yeah..."

"I know."

"What?!"

"I know," Cas said nonchalantly, watching Dean.

"Bu- then why didn't you go all smiting on my ass, then?!"

Cas smiled, calmly albeit sadistically. "I knew the guilt would eat away at you. Your conscience was your own punishment, Dean."

Dean growled something, and he felt warmth envelop his body. This is how he knew Cas had his wings invisibly extended, and they were wrapped around his body.

"I love you," the angel told him, "and that dirty assbutt Phoenix motherfucker got what was coming to him."

Dean choked in surprise and stared at Cas, slightly turned on by his language. "Where the hell'd you learn to talk like that?"

Cas grinned. "Westerns."


End file.
